Process of producing transformation products of acrylic acid or its derivatives



Patented Mar. 16, 1937 awash PROCESS OF PRODUCING TRANSFORM- TION PRODUCTS OF ACRYLIC ACID OB ITS DERIVATIVES Walter Bauer and Adolf Gerlach, Darmstadt, Germany, a'ssignors, by mesne assignments, to Riihm & Haas Company, Philadelphia, Pa, a corporation of Delaware No Drawing. Application December 19, 1928,

Serial No. 327,113. Renewed March 20, 1934.,

In Germany-January 24. 1928 8 Claims.

Our invention consists in a new process of making polymerization products of acrylic acid and acrylic acid derivatives containing the following characteristic nuclear structure ,We have discovered that technically usefulpolymerization products of acrylic acid and acrylic acid derivatives containing the following characteristic nuclear structure can he made by saidcomp'ounds being treated with'gaseo'us oxygen. By the application of heat or pressure, or both, the reaction is expedited. In the place of oxygen, also oxygen containing gases, e. g. air, or substances, which under certain conditions will split ofi oxygen, e. g. organic superoxides, can be employed. The polymerization can he successfully performed with small amounts of the said substances. Also suitable supplemental agents can be added. For instance, we have found that the addition of organic solvents, e. g. acetone, or the like, is especially advantageous.

Example 100 kg. of acrylic acid ethyl ester are mixed-with 100- kg. of acetone and in an iron vessel are heated to boiling temperature while continually oxygen is passed through the mixture. A solution of great viscosity is formed. After the heating has {been continued for 'about twenty hours, the odor of the acrylic acid ethyl ester has completely dis-, appeared. The resultlngsolution can be used for technical purposes. By the acetone bein distilled off, a solid polymerization product of acrylic acid ethyl ester-is obtained.

For instance, esters of acrylic acid, such as the ethyl ester may be used. Likewise the term oxygen as used herein, includes not only oxygen itself, but gases containing oxygen and substances adapted to split oil oxygen.

(on. soo -2) I We claim:-

l. Intthe manufacture of polymerization prod ucts from the ethyl ester of acrylic acid, the process' which comprises mixing together approximately equal parts of said ethyl ester and acetone, heating the mixture to boiling and simultaneously passing a current bf gaseous omgen through the heated mixture until said polymerization is eflected and then distilling oh the acetone and recovering the solid polymerization product thus obtained.

2. In the manufacture of polymerization products from the ethyl ester of acrylic acid, the process which comprises mixing said ester with acetone, heating the mixture to boiling and passing a current of gaseous oxygen through the heated mixture until said polymerization is eflected.

3. In the manufacture of polymerization prodnote from theethyl ester of acrylic acid, the process which comprises mixing said ester with an organic solvent, heating the mixture to hoiling and passing a current of gaseous oxygen through the heated mixture until said polymerization is efiected. e 4. In the manufacture of polymerization prodnote from an ester of acrylic acid the process which comprises mixing said ester with errorganic solvent, heating the mixture to boiling, and passing a current of oxygenthrough the heated mixture until said polymerization is efiected.

5. In the manufacture of polymerization products of an aliphatic ester of acrylic acid the step which comprises subjecting the ester to polymerizing influences in the presence of an organic peroxide.

6. The process which comprises polymerizing an ester of acrylic acid in the presence of oxygen. 

